Gary Allan Herzberg was born and raised in La Mirada, California,[1] to Harley and Mary Herzberg.[2] To ensure that the family would focus on music, Allan's mother insisted that the family's guitars would always remain visible in the home. At age 13, Allan began playing in honky tonks with his father.[1][3] Two years later, he was offered his first recording contract, from A&M Records, but rejected the deal. His parents wanted him to finish his education and his father felt that Allan had yet to develop his own distinctive style.[4] Despite his commitment to finishing school, Allan reflects that he was rarely alert in class. "I played the bars at night, I was half asleep when I got to school. I thought sleep was what you did when you go to school."[4]

After graduating from La Serna High School in Whittier, California, Allan continued to play in the bars with his band, the Honky Tonk Wranglers. Many of the venues they played were packed, and promoters often tried to move them to larger clubs. The moves would have required him to stop playing some of the older country music, such as covers of George Jones songs, so Allan refused.[3]

In 1987, Gary married his first wife, Tracy Taylor. They since divorced. He married model Danette Day on November 28, 1998, in South Carolina and they divorced in June 1999.[5] His third wife, Angela[6] (whom he wed on June 5, 2001), died by suicide on October 25, 2004.[6][7][8]

Allan was introduced to songwriter/producer Byron Hill on August 28, 1993, by a mutual friend and talent-scout Jim Seal, at a bar called the Lion D'or in Downey, California, where Allan was already regularly performing. Seal and Hill had asked Allan if they could showcase an unsigned act that they were developing there. Hill had arranged to bring the head of A&R from a major label to the show to see this other act perform. Allan kindly let them use his stage for the event, giving the new act the opening performance slot that night. Hill promised Gary that they would make sure the A&R person remained there to see his portion of the show. Everyone was knocked out with Allan's performance, and very impressed with his voice. From that point on, Byron Hill began sending Gary songs. Without any serious funding at the time, Hill arranged for Allan to go into Seal's small studio in California to try his vocals on some of existing demo tracks that Byron had sent to Gary from Nashville, Tennessee. Meanwhile, Hill became head of A&R at BNA Entertainment on October 29 of that same year and immediately wanted to sign Allan to BNA, but the then current roster conditions and other circumstances related to the planned restructuring of RCA/BNA Nashville stood in the way.[9]

In the meantime, Allan took a job selling cars. He left a demo tape in the glove box of a truck purchased by a wealthy couple. When the couple discovered that he was the singer, they wrote him a check for $12,000.[4] This independent funding allowed Allan to go to Nashville to record some of the songs that were on that early demo tape with Byron Hill as producer.[9] On September 11, 1995, they worked at Javelina Studios for a couple of days on the four songs that Hill immediately showed to labels. Allan's recordings brought serious responses from several labels including Mercury, RCA, and Decca.[9] A meeting was then held at a Nashville hotel among Hill, Allan, and friend of Allan's, who was a program director for a radio station in California.[9]

The meeting was to arrange two showcases in Los Angeles, California, to put Allan on stage at two of the radio station's regular nights at a local club. Byron arranged for staffers at the Nashville office of Decca Records to attend the first showcase held on November 1, 1995. Decca immediately wanted to sign Allan, and knowing that Byron was lining up other labels to see Gary, Decca asked them to cancel the second showcase. A rep from RCA was already booked to see the second showcase the following week, but the "bird-in-hand" deal offer was too tempting for both Byron and Gary, so they committed to the Decca offer.[9] Decca staffer Mark Wright and Byron Hill co-produced Gary's first three albums for Decca beginning sessions on March 11, 1996 for Used Heart for Sale, then It Would Be You, both of which yielded top five singles, and later Smoke Rings in the Dark (which also included Tony Brown as a co-producer). It was during the recording of the first album that they recorded "It Must Have Been Ol' Santa Claus", as an added track to be packaged on various MCA/Decca Christmas compilations.[9] Then Byron and Gary got a personal call from Harry Connick, Jr., the writer of the song, thanking them for the recording, during which he added a few of his New Orleans Jazz style "very cool man!" compliments. The Christmas recording has been since released on at least four compilations. The merger of Polygram, Decca, and MCA Records marked the closing of Decca and Gary was moved to MCA Records.[9]

Allan's second studio album, It Would Be You, was released in 1998. Although he has been writing songs since his teen years,[4] the singer has not really hesitated to bump his work from his albums in favor of those written by other songwriters that he respects. For this album, Allan replaced one of his songs with "No Judgement Day", written by Allen Shamblin. Even though that song was a hidden acoustic track, radio stations started giving it some heavy airplay.[4] "No Judgement Today" tells the story of a restaurant owner from a small town in Texas, where ex co-workers killed him in search of money, for drugs and alcohol. The album's title track became Allan's second hit to reach the Top 10 on the U.S. country charts, remaining there after 21 weeks of radio play, "way beyond the tenure of most disposable radio hits."[10] In early-1999, Decca Records folded, and when Allan moved to the parent label, MCA Nashville, the It Would Be You album was left in limbo.[3]

Allan was named as "Country Music's Sexy Star" by People Magazine. He also delved into the acting world in the TV mini-seriesShake, Rattle, & Roll, in which he would play the lead role of Eddie Cochran. He followed that role with a part in the CBS TV series Pensacola: Wings of Gold, but describes his acting experience as "tedious."[4]

In 1999, Allan released his third studio album Smoke Rings in the Dark.[1] This was an album that he recorded while in the midst of divorcing from his second wife, Versace model Danette Day, after only seven months of marriage.[4] Unlike his first two albums, Smoke Rings in the Dark made fuller use of background singers and stringed instruments, "resulting in a lusher, fuller sound."[11] The new album avoided the "devil-may-care brashness" of the first two, instead presenting a tone balanced between youthful optimism and "the knowledge that some of life's experiences exact a high toll."[11]Smoke Rings in the Dark was certified platinum, and it included two successful singles, including its title track.

The singer's fourth studio album Alright Guy was released in 2001.[1] It contained the singles "The One," "Man of Me," and "Man to Man," the latter of which became his first number one hit on the U.S. Billboard country charts.[12] That same year, Allan married for the third time, to Angela, a flight attendant who he met on an airplane.[13]

Despite his previous success and eight years in the music business, Allan was nominated for the Country Music Association's Horizon Award, typically given to newcomers, in 2003. The same year, he released his fifth studio album See If I Care. Allan had to be controversial to keep the album's title. Also, he thought that title had epitomized his attitude towards the music business, and that he would continue to make the music that he wanted to make regardless of whether the record label chose to back him or people chose to buy the album.[14]See If I Care included Allan's second and third number one singles with "Tough Little Boys", and "Nothing On but the Radio."[12][15] "Songs About Rain" was a Top 15 hit.

In 2003, Allan and his wife, Angela Herzberg, moved to Tennessee from California. On October 25, 2004, Angela committed suicide after suffering from depression and migraines. Allan initially put his career on hold, but soon returned to music to deal with the loss of his wife. This resulted in 2005's "heart-wrenchingly personal album," Tough All Over.[13] He included several songs which he wrote or cowrote, including "Puttin' Memories Away" and "I Just Got Back from Hell," which dealt directly with his grief.[16] Several years later, Gary discussed his wife's suicide on The Oprah Winfrey Show.

Allan's first Greatest Hits collection was released on March 6, 2007. A Number One album on the Billboard Top Country Albums charts, the album reprised the greatest hits from his first six albums, as well as two new songs. One of these, titled "A Feelin' Like That", was co-written by David Lee Murphy and Ira Dean (the latter a former member of Trick Pony); the single peaked at No. 12 on the country singles charts.

The album Living Hard was released on October 23, 2007. Serving as its lead-off single was the song "Watching Airplanes," which spent more than thirty weeks on the country charts, where it reached a peak of No. 2 and went No. 1 on the Mediabase Chart. The song's music video was filmed during live concerts, including one at the Red Rocks Amphitheatre in Morrison, Colorado. Second single "Learning How to Bend" – co-written by Allan – quickly became another hit song, peaking at No. 13. The video was filmed during a live performance at the House of Blues in Atlantic City, New Jersey. Following this song is third single "She's So California," which Allan co-wrote with Jaime Hanna (of Hanna-McEuen) and Jon Randall, and it peaked at No. 24, becoming his first single to miss the top 20 since "Lovin' You Against My Will" in 2000.

Allan's ninth studio album, Set You Free, was released on January 22, 2013.[19] Its first single, "Every Storm (Runs Out of Rain)", was released to country radio on September 17, 2012 and reached Number One on the Country Airplay chart on February 9, 2013, giving Allan his fourth Number One country hit and his first since "Nothing On but the Radio" in December 2004. In an interview with Broadway's Electric Barnyard, Allan spoke about co-writing with women for the new release. It was the first time in his career he had done so, and he described it as an interesting experience.[20] The album's second single, "Pieces", was released to country radio on February 25, 2013. The third single, "It Ain't the Whiskey", was released on September 23, 2013.

In March 2015, Allan released a new single entitled "Hangover Tonight". This song would serve as the lead single to his upcoming tenth studio album, entitled Hard Way.[21] In May 2016, the album's second single "Do You Wish It Was Me?" was sent to country radio. The third single is "Mess Me Up", released to country radio in May 2017. None of these three singles, however, had performed as expected on the charts, resulting in EMI Nashville delaying the release of the album.[22]

Allan's voice is described as "raspy and unpolished."[3] The New York Times describes his music as "elegant, often deadpan songs [that] tend toward manly understatement."[24] His sound is heavily influenced by the Bakersfield scene, especially Buck Owens and Merle Haggard. He prefers this sound to that of the more pop country that is prevalent on country radio, because "the songs have got to have soul, have real meaning....Country music is...what happens during the week. Rock 'n roll is about what happens at the weekend."[4] Because his sound is different from many of the current crop of country singers, as their sound is considerably more pop or rock, Allan has, at times had difficulty getting radio to play his singles. He says he has to "walk a real fine line" to "make sure that I get traditional stuff on the radio."[3]